Rhamnazin

Rhamnazin
Names


IUPAC name 3,4′,5-Trihydroxy-3′,7-dimethoxyflavone
Systematic IUPAC name 3,5-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Other names 3′,7-Dimethylquercetin 3,5,4′-Trihydroxy-7,3′-dimethoxyflavone 5,3′,4′-Trihydroxy-3,7-dimethoxyflavone Flavone, 3,4′,5-trihydroxy-3′,7-dimethoxy-
Identifiers
CAS Number	552-54-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:133721^N
ChEMBL	ChEMBL457148^N
ChemSpider	4478873^N
PubChem CID	5320945
UNII	276CK9GP9Y^Y
CompTox Dashboard (EPA)	DTXSID00203695
InChI InChI=1S/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-10(18)12(5-8)23-2/h3-7,18-19,21H,1-2H3^N Key: MYMGKIQXYXSRIJ-UHFFFAOYSA-N^N InChI=1/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-10(18)12(5-8)23-2/h3-7,18-19,21H,1-2H3 Key: MYMGKIQXYXSRIJ-UHFFFAOYAP
SMILES COC1=CC(=C2C(=C1)OC(=C(C2=O)O)C3=CC(=C(C=C3)O)OC)O
Properties
Chemical formula	C₁₇H₁₄O₇
Molar mass	330.292 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Rhamnazin is an O-methylated flavonol, a type of chemical compound. It can be found in Rhamnus petiolaris,^[1] a buckthorn plant endemic to Sri Lanka.

Metabolism

The enzyme 3-methylquercetin 7-O-methyltransferase uses S-adenosyl methionine and isorhamnetin to produce S-adenosyl homocysteine and rhamnazin.

The enzyme 3,7-dimethylquercetin 4'-O-methyltransferase uses S-adenosyl methionine and rhamnazin to produce S-adenosyl homocysteine and ayanin.

References

^ Wagner, H.; Ertan, M.; Seligmann, O. (1974). "Rhamnazin- und rhamnetin-3-O-trioside aus Rhamnus petiolaris". Phytochemistry (in German). 13 (5): 857–860. doi:10.1016/S0031-9422(00)91151-8.

External links

Rhamnazin on the Extrasynthese catalogue

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)